The antithyroid drug methimazole (MMI) reacts with molecular iodine to form, in a multistep process, 1-methylimidazole as final product. In this process, the charge transfer complex MMI-I2 and the ionic disulfide [(C4H6N2S–)2]2+ (1, dication MMI disulfide) have been isolated and their X-ray crystal structures solved. Dication MMI disulfide perchlorate acts effectively both in reducing I2 to I- ions and in showing antioxidant properties in inactivating the enzyme lactoperoxidase compound I.
Interaction of Methimazole with I2: X-ray Crystal Structure of the Charge Transfer Complex Methimazole-I2. Implications for the Mechanism of Action of Methimazole-Based Antithyroid Drugs
ISAIA, FRANCESCO;ARAGONI, MARIA CARLA;ARCA, MASSIMILIANO;LIPPOLIS, VITO;MEDDA, ROSARIA;
2008-01-01
Abstract
The antithyroid drug methimazole (MMI) reacts with molecular iodine to form, in a multistep process, 1-methylimidazole as final product. In this process, the charge transfer complex MMI-I2 and the ionic disulfide [(C4H6N2S–)2]2+ (1, dication MMI disulfide) have been isolated and their X-ray crystal structures solved. Dication MMI disulfide perchlorate acts effectively both in reducing I2 to I- ions and in showing antioxidant properties in inactivating the enzyme lactoperoxidase compound I.
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